Further Investigation of the Nature of the C‐Li Bond. Structures of a Phenylthiomethyllithium Complex and ofa Methylthiomethyllithium Complex | Zendy

Amsturz René | Zendy; Laube Thomas | Zendy; Schweizer W. Bernd | Zendy; Seebach Dieter | Zendy; Dunitz Jack D. | Zendy

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Further Investigation of the Nature of the C‐Li Bond. Structures of a Phenylthiomethyllithium Complex and ofa Methylthiomethyllithium Complex

Author(s) -

Amsturz René,

Laube Thomas,

Schweizer W. Bernd,

Seebach Dieter,

Dunitz Jack D.

Publication year - 1984

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19840670129

Subject(s) - chemistry , tetramethylethylenediamine , ring (chemistry) , crystallography , atom (system on chip) , thioanisole , crystal structure , unit (ring theory) , stereochemistry , medicinal chemistry , biochemistry , mathematics education , mathematics , organic chemistry , computer science , embedded system , catalysis

Phenylthiomethyllithium/ N , N , N ′, N ′‐tetramethylethylenediamine (TMEDA) (1:1) is shown by X‐ray analysis to be dimeric in the crystalline state. The structural unit contains a six‐membered ring in which each Li is bonded to the terminal C atom of one thioanisole and to the S atom of the other, as well as to the two N atoms of a TMEDA. Methylthiomethyllithium/TMEDA (1:1) is also dimeric, but the structural unit contains a four‐membered ring in which each Li is bonded to two C atoms and to the two TMEDA N atoms. An error has been detected in an earlier published electron‐density difference map for 2‐lithio‐2‐phenyl‐1, 3‐dithiane/TMEDA/THF (1:1:1). The conclusion drawn then that this complex exists as a tight ion‐pair in the crystal is now retracted.

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